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Understanding Organic Reactions

Topic Review on "Title":

Terminology of Organic Reactions
A mechanism is a complete step-by-step description of the bond breaking and the bond forming steps.  Stochiometry is the relationship between reactants and products in a chemical reaction.  Thermodynamics is the study of the energy changes that accompany the physical and chemical changes.  Kinetics is the study of the rates of chemical reactions.  Transition state is the energy state between reactants and products.  Activation energy is the energy needed to initiate a chemical reaction.  Hammond postulate is the structure of a transition state is most similar to the structure of the closest stable species.  Kinetic vs. thermodynamic control is kinetic product predominates at low temperature and thermodynamic product predominates at high temperature.  Reactive intermediate is a short-lived species that is an intermediate in a chemical reaction.  Catalyst is a compound that increases the rate of reaction without being consumed.  Solvent effect is the effect that a solvent has on the rate of reaction.

Reaction of Alkyl Halides
Alkyl halides can be substituted with nucleophiles to form other compounds.  Alkyl halides react with potassium hydroxide to yield alkenes.  Alkyl halides with lithium to yield alkyl lithium or magnesium to form Grignard reagents.

Reaction of Alkenes
Alkenes react with hydrogen halide to form alkyl halides.  Hydrolysis of alkenes form alcohols.  Halogenation of alkenes yield dihaloalkanes.  Hydrogenation of alkenes give alkanes.  Alkenes are oxidized with potassium permanganate to form diols or with ozone to form aldehydes and ketones.

Reaction of Alkynes
Alkynes react with hydrogen halide and halogenated to give alkyl halides.  Alkynes are hydrogenated to give alkanes.  Alkynes are oxidized with potassium permanganate to give diketones or with ozone to give carboxylic acids.

Reactions of Aromatics
Aromatic compounds are halogenated to give halobenzenes, nitrated to give nitrobenzenes, and sulfonated to yield benzenesulfonic acids.  Aromatic compounds undergo Friedel-Craft alkylation to give alkylbenzenes and undergo Friedel-Craft acylation to give ketones.

Reaction of Amines
Amines react with alkyl halides to yield larger amines and react with hydrogen halides to give ammonium salts.  Amines react with acid halides to give amides and react with sulfonyl chloride to yield sulfonamides.

Reactions of Alcohols
Alcohols are deprotonated with metal to give alkoxides.  Alcohols react with hydrogen halide, phosphorus trihalide, or phosphorus oxychloride to give alkyl halides.  Dehydration of alcohols yield alkenes.  Zero and primary alcohols are oxidized form aldehydes. Zero and primary alcohols are oxidized to form carboxylic acids.  Secondary alcohols are oxidized to yield ketones. Tertiary alcohols cannot be oxidized. Alcohols react with carboxylic acids, in the presence of acid, to yield esters.

Reactions of Aldehydes and Ketones
Reduction of aldehydes and ketones yield alcohols and alkanes.  Reaction of aldehydes and ketones with alkyl lithium or alkyl magnesium halide give alcohols.  Aldehydes and ketones are treated with an amine derivative and acid to give imines.  Reductive amination of aldehydes and ketones produce larger amines.  Aldehydes are oxidized to carboxylic acids.

Reactions of Carboxylic Acids
The reduction of carboxylic acids produce alcohols.  Carboxylic acids react with thionyl chloride to give acid chlorides.  The reaction of carboxylic acids with alcohols and acid  give esters.  Carboxylic acids react with acid halides to give anhydrides.

Reactions of Acid Halides
Hydrolysis of acid halides yield carboxylic acids.  Acid halides react with alcohols to form esters.  The reaction of acid halides with amines form amides.  Acid halides are reduced with to alcohols and aldehydes.  Acid chlorides react with dialkyl lithium cuprates to yield ketones.

Reactions of Esters
Hydrolysis of esters yield carboxylic acids and alcohols.  Reduction of esters produce alcohols.  Esters react with amines to yield amides and alcohols.

Reactions of Anhydrides
Hydrolysis of anhydrides produce carboxylic acids.  Anhydrides react with alcohols to yield esters and carboxylic acids.  Anhydrides react with amines to give amides and carboxylic acids.

Reactions of Amides
Amides are hydrolyzed with water and acid to give carboxylic acids and ammonium ions.  Amides are hydrolyzed with water and base to yield carboxylate anions and amines.  Reduction of amides produce amines.  Dehydration of amides give nitriles.


Rapid Study Kit for "Title":
Flash Movie Flash Game Flash Card
Core Concept Tutorial Problem Solving Drill Review Cheat Sheet

"Title" Tutorial Summary :
The terminology of organic reactions is defined as mechanism, stoichiometry, thermodynamics, kinetics, transition state, activation energy, Hammond postulate, kinetic vs. thermodynamic control, reactive intermediate, catalyst, and solvent effect.  Alkyl halides can be substituted with nucleophiles, can undergo elimination, react with lithium, and react with magnesium.  Alkenes react with hydrogen halide, water, halogen, and hydrogen.  Alkenes can be oxidized with potassium permanganate, and ozone.  Alkynes react with hydrogen halide, halogen, and hydrogen.  Alkynes are oxidized with potassium permanganate, and ozone.  Aromatic compounds are halogenated, nitrated, and sulfonated.  Aromatic compounds undergo Friedel-Craft alkylation and Friedel-Craft acylation.  Amines react with alkyl halides, hydrogen halides, acid halides, and sulfonyl chlorides.  Alcohols react with metal, are converted to alkyl halides, are dehydrated, are oxidized, and react with carboxylic acids.  Aldehydes and ketones are reduced to alcohols and alkanes.  Aldehydes and ketones under reaction with organometallics and primary amines.  Aldehydes and ketones undergo reductive amination.  Aldehydes are oxidized.  Carboxylic acids are reduced to alcohols, react with thionyl chloride, react with alcohols, and react with acid halides.  Acid halides undergo hydrolysis, react with alcohols, react with amines, are reduced to alcohols, are reduced to aldehydes, and react with dialkyl lithium cuprate.  Esters are hydrolyzed, reduced to alcohols, and react with amines.   Anhydrides are hydrolyzed, react with alcohols, and react with amines.  Amides are hydrolyzed with water and acid or base, reduced, and dehydrated.

Tutorial Features:

This tutorial provides the comprehensive coverage of the chapter with easy introduction and simple illustration. It features:

  • Concept map showing interconnections of new concepts in this tutorial and those previously introduced.
  • Definition slides introduce terms as they are needed.
  • Visual representation of concepts.
  • Use of colors to emphasis points.
  • Outline of terminology.
  • Detailed stepwise explanations and animations of reactions.
  • Examples worked out step-by-step throughout the tutorial.
  • A concise summary is given at the conclusion of the tutorial.

"Title" Topic List:

Terminology of Organic Reactions

Reactions of Alkyl Halides

  • Substitution with Nucleophiles
  • Elimination with potassium hydroxide
  • Reaction with Lithium
  • Reaction with Magnesium

Reactions of Alkenes

  • Addition of Hydrogen Halide
  • Addition of Water
  • Addition of Halogen
  • Addition of Hydrogen
  • Oxidation with Potassium Permanganate
  • Oxidation with Ozone

Reactions of Alkynes

  • Addition of Hydrogen Halide
  • Addition of Halogen
  • Addition of Hydrogen
  • Oxidation with Potassium Permanganate
  • Oxidation with Ozone

Reactions of Aromatic Compounds

  • Halogenation
  • Nitration
  • Sulfonation
  • Friedel-Craft Alkylation.
  • Friedel-Craft Acylation

Reactions of Amines

  • Reaction with Alkyl Halides
  • Reaction with Hydrogen Halides
  • Reaction with Acid Halides
  • Reaction with Sulfonyl Chlorides

Reactions of Alcohols

  • Reaction with Metal
  • Converted to Alkyl Halides
  • Dehydration
  • Oxidation
  • Reaction with Carboxylic Acids.

Reaction of Aldehydes and Ketones

  • Reduction to Alcohols
  • Reduction to Alkanes
  • Reaction with Organometallics
  • Reaction with Primary Amines
  • Reduction Amination
  • Oxidation of Aldehydes

Reaction of Carboxylic Acids

  • Reduction to Alcohols
  • Reaction with Thionyl Chloride
  • Reaction with Alcohols
  • Reaction with Acid Halides

Reaction of Acid Halides

  • Hydrolysis
  • Reaction with Alcohols
  • Reaction with Amines
  • Reduction to Alcohols
  • Reduction to Aldehydes
  • Reaction with Dialkyl Lithium Cuprate

Reactions of Esters

  • Hydrolysis
  • Reduction to Alcohols
  • Reaction with Amines

Reactions of Anhydrides

  • Hydrolysis
  • Reaction with Alcohols
  • Reaction with Amines

Reactions of Amides

  • Hydrolysis with Acid
  • Hydrolysis with Base
  • Reduction
  • Dehydration


See all 24 lessons in college chemistry, including concept tutorials, problem drills and cheat sheets:
Teach Yourself Organic Chemistry Visually in 24 Hours

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